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In Nicholas Ray’s 1955 masterpiece Bigger Than Life, James Mason plays a cash-strapped teacher who begins receiving cortisone shots that transform him from a harried everyman to an insane narcissist. At the height of his manic dementia, Mason is ready, even willing, to sacrifice his son to prove a point that matters only to him.

Murder is always transgressive, but there’s something particularly bracing about watching a grown man contemplate murdering a little boy, especially when that little boy is his own son. There is no distance or irony in Mason’s performance: He takes us to the very edge before pulling back at the last possible minute.

Post-cortisone, James Mason’s personality bears a distinct resemblance to that of the great Sideshow Bob. He’s haughty, aristocratic, filled with richly merited contempt for what H.L Mencken dubbed “the booboisie,” and more than willing to murder a small child if need be.

In crafting the iconic villain of Sideshow Bob, the writers and producers drew heavily from the effete persona Kelsey Grammer developed over the course of several million decades playing Frasier Crane on Cheers and then Frasier. The show unleashes the aristocratic rage lurking underneath Grammer’s impeccable good manners and tony speech. It connects with the Killer Klown behind the tweedy veneer.

Sideshow Bob represents something unique in television history. He is an exemplar of over-class rage, a snob with a vendetta. In one of the show’s most inspired sick jokes, Sideshow Bob is ultimately on the side of right. He wants to elevate the level of discourse on television and respect children’s intellects even if he has to kill and frame and maim to do so.

In “Black Widower,” Sideshow Bob does something even more repellent: He gets engaged to Aunt Selma. They are a study in contrasts: a highbrow snob who sneers derisively at the foibles of the hoi polloi and a raspy-voiced misanthrope whose conception of great art is a MacGyver marathon. The writers and animators take great care to make Aunt Selma as repulsive as possible, taking particular care where her hairy legs are concerned.

“Black Widower” opens on an almost wistful note, with Sideshow Bob coming to dinner at The Simpsons’ as Aunt Selma’s new boyfriend and recounting a prison experience that sounds less hellish than mildly unpleasant. Once again the genius is in the details, like the way the conjugal trailers rock with the sound of jailbird love-making as Sideshow Bob’s violin provides sweet mood music outside.

Bart is understandably distrustful of Sideshow Bob, but the rest of the world eagerly embraces him, even Krusty the Klown. Only Bart holds onto a grudge. Otherwise, the world is willing to give him another chance.

How great is Grammer as Sideshow Bob? He manages to make a prissy elitist scary. There is a musicality and a poetry to his performance, an almost hypnotic rhythm to the way he delivers a line like, “Ah, fire: scourge of Prometheus, toaster of marshmallows, eradicator of dead wood.” In depth, richness, multi-dimensionality and language, Sideshow Bob might just be the most Shakespearean character in The Simpsons universe.

He’s an aristocrat in a slobbish realm. Sideshow Bob finds his ultimate hell in the person of Aunt Selma and the ultimate crucible: enduring MacGyver. A look of almost uncontrollable horror and contempt dances upon Sideshow Bob’s face when MacGyver comes on. It takes every bit of willpower he possesses to refrain from screaming his contempt for the show from the mountains. Finally, he can’t take it anymore.

When Selma asks him to praise MacGyver, the best he can come up with is a poisonously sarcastic, “That was a well-plotted piece of non-claptrap that never made me want to retch.” Selma is devastated. “Black Widower” is spectacularly funny, but it’s also poignant and sad in the way Patty and Selma episodes invariably are. As Patty notes, Aunt Selma has a crazy obsession with not dying alone where she has reconciled herself to a life of infinite loneliness.

So there’s something poignant about the notion that a creature as repulsive as Selma might find love, even if we realize that she’s ultimately doomed. In courtship mode, Sideshow Bob is hilariously smarmy as he writes to his hapless mark, “Your latest letter set off a riot in the maximum security ward of my heart.” In non-smarmy mode, Bob drips with contempt for everyone and everything.

“Black Widower” is shot more like an episode of Alfred Hitchcock Presents than a conventional cartoon. It’s cinematic in its aesthetic, casually ambitious in the sheer amount of jokes, gags, and ideas it fits into 22 minutes while still sustaining a fairly advanced mystery plot centering on Bob’s plans to kill Selma through a gas explosion set off by one of her beloved cigarettes.

It’s a testament to how thoroughly Sideshow Bob and Grammer’s performance dominate the episode that Bart, our ostensible boy detective hero, barely registers. Then again, the bad guy always gets the best lines. Where The Simpsons and Sideshow Bob are concerned, he also gets the best episodes and this funny, scary, and quietly sad episode is right up there.

Stray observations:

Boy, that swipe at Dinosaurs felt more than a little heavy-handed. Like, Dinosaurs-level heavy-handed

I love how angry Homer becomes when Sideshow Bob accuses him of forgetting the first two noble truths of the Buddha. Apparently that’s a real point of pride for him.

“I need a man and I cannot find one among the law-abiding” is a great line, but what really sells it is the mildly dispirited way it is delivered.

I cannot say how often I have uttered a variation on, “Snake, I am going to miss you most of all!”

“You’re living proof that our revolving-door prison system works!”

“Although kissing you would be like kissing some divine ashtray, that’s not what I have in mind.”

I kind of like Aunt Selma in love. It’s very humanizing. “May you drive safely and find true love.”

“Hey, if they ever open the books on this telethon, I’m right back in there.”

“I’ve already run through eight of the 10 dollars they gave me when I left prison!”